title: Formal homoiodo allylsilane annulations: dual total syntheses of (±)-hirsutene and (±)-capnellene.
abstract: Dual total syntheses of (±)-hirsutene and (±)-capnellene, two typical linear triquinane sesquiterpenes, were achieved via a formal [3 + 2] annulation strategy, as illustrated schematically. Cyclic homoiodo allylsilanes were employed as key bifunctional synthons in the synthesis, which were readily prepared from the corresponding cyclopropanated cyclopentenones. A formal [3 + 3] annulation approach for the elaboration of the bicyclic framework of the Eudesmane sesquiterpenoids based on this type of synthon was also developed.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, PR China.
authors.forename: Shou-Jie
authors.initials: SJ
authors.lastname: Shen
authors.forename: Wei-Dong Z
authors.initials: WD
authors.lastname: Li
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D012821:Silanes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; D012821:Silanes; C511847:allylsilane; C548741:capnellene; C486985:hirsutene